5-aminoisophthaloylacetonitrile



Patented Aug. 7, 1951 UNITED STATES PATENT OFFICE -AMINOISOPHTHALOYLACETONITRILE Leslie M. Schenck, Westfield, N. J., assignor to General Aniline & Film Corporation, New York, N. Y., a corporation of Delaware No Drawing. Application October 29, 1949, Serial No. 124,518

'3 Claims. (Cl. 260-465) 1 2 This invention relates to a new composition 01' since it is possible to mix them together. The matter and to a method for preparing it. hydrolysis step may be accomplished at a temp-Aminobenzoylacetonitrile is known and has perature lower than the reflux temperature. been prepared by a Friedel-Crafts reaction which. Alkaline reactants other than sodium hydroxide gives a poor yield. The present invention is di- 5 may be used for the hydrolysis. Other inert s01- rected to the production of 5-aminoisophthaloylvents may be substituted as may other enolizing acetonitrile and for a method of producing it. agents such as other sodium alcoholates as will It has been found that reacting S-carbethoxybe apparent to those skilled in the art. aminoisophthaloylchloride with ethylcyanoace- The reaction may be represented as follows:

NHCOOCnHs NHCOOCzHs soon CIHsOCOCHzCN 1100c 0001: C001 C001 ,212

COOCnH COHCN COCHzON OCHCN OCHzCN OOCaHs tate and an enoiizing agent and hydrolyzing the The product is useful in preparing magenta product, 5-aminoisophthaloylacetonitrile is 012- color formers for color film. tained. I claim:

The following example illustrates a preferred 1. 5-aminoisophthaloylacetonitrile. embodiment of the invention but variations and 2. A process for producing S-aminoisophthalsubstitutions may be made within the scope of oylacetonitrile which comprises reacting 5- the appended claims. carbethoxyaminoisophthaloylchloride with eth- Exampze ylcyanoacetate and an enolizing agent and bydrolyzing the product.

100 pa ts 1 5%arbeth0xyamin0i50phthalic 3. A process for producing 5-aminoisop'hthal acid is added to a solution of 220 parts of benzene oylacetonitrile which comprises reacting 5- a d 23 Parts thionylchloride- The mixture 15 carbethoxyaminoisophthalic acid with thionyl refluxed until the evolution of hydrogen chloride chleride, reacting t hl id th formed with ceases and the volatile solvent is then removed ethylcyanoacetate i th presence of di m in vacuum, the residual acid chloride is dissolved methylate and hydrolyizing the product in an in 260 parts acetone and added during one hour amaline di at a temperature below 5 C. to a mixture 460 LESLIE SCHENCK parts acetone, 1'75 parts ethylcyanoacetate and 81 parts 95% sodium methylate. After stirrin REFERENCES CITED l i r ed g gg g gf i gg g g g izggfig f g g The following references are of record in the addition of acetic acid. The crude material is me of thls patent hydrolyzed by refluxing for /2 hour with a slight UNITED STATES PATENTS excess of sodium hydroxide solution. Upon cool- Number Name Date ing the product is precipitated by slowly adding 1951x421 Wah] Man 13, 1934 acetic acid. The product is a white crystalline 2,392,167 Long et Jan 1, 1946 material having a melting point of 211-212 C.

In the above example, the acid chloride may OTHER REFERENCES be precipitated with petroleum ether instead of Dorsch et al., J. Am. Chem. Soc., vol. 54, pp. removing the volatile solvents. Furthermore, it 2960-2964 (1932). is not necessary to dissolve the acid chloride in Long et al., J. Am. Chem. Soc., vol. 69, pp. 990- acetone and add slowly to the other reactants 995 (1947). 

1. 5-AMINOISOPHTHALOYLACETONITRILE. 